La Siesta Resort & Villas

Walk-In Water at Mile Marker 80

The Florida Keys are famously short of swimmable beach. The reef takes the surf, the shoreline turns to rock and mangrove, and most oceanfront resorts hand you a seawall and a ladder. La Siesta is one of the exceptions: private beaches you walk into, on the Atlantic side of Islamorada at 80241 Overseas Highway. The property is laid out low and green, cottages and casitas along the sand, villas set behind, palms doing most of the shading. Fifty-odd keys in total, which keeps it closer to a compound than a hotel, and the water is the organising principle of the whole plan.

Why It Works

Three things settled it. The beach, first, for the reason above. Then the equipment: kayaks, paddleboards and bikes come with the room rather than with a rental desk, which changes how a family actually uses a day here. And finally the dock, with slips for boats and jet skis, in a village where dockage decides where people stay. Islamorada has flashier addresses and older ones. This is the one that lets four people in a group do four different things before lunch and still meet on the same strip of sand.

Why This Location

Mile marker 80 puts you in the northern half of Islamorada, ocean side, which means sunrise over the water from the cottages and a short hop across the highway for the bayside sunset. The village’s fishing fleet and its fish houses run either side of you along the Overseas Highway. Theater of the Sea sits a few minutes north, Robbie’s tarpon dock and the backcountry guides a few minutes south, and Founders Park, with its pool and beach, is close enough to walk for an afternoon. The reef is straight out front, which is what the paddleboards are for.

Fast Facts

• Price: €€€

• Vibe: Barefoot, green, family-shaped, unhurried

• Rooms: Around fifty keys in five categories: Beachfront Cottages, Beachfront Casitas, Coastal Villas, Ocean Suites and Tropical Garden Suites

• Best For: Families, multi-generation groups, boat owners, travellers with a dog

• Our Favorite Thing About the Hotel: The four private villas that come with a butler, which is an unusual thing to find attached to a Keys beach resort

• Dining: SIDECAR, the on-site tiki bar, for tropical drinks, light lunches and afternoon snacks; a dozen more tables across the sister resorts, reachable by the water taxi

• Amenities: Walk-in private beaches, pool, dock slips for boats and jet skis, kayaks, paddleboards and bikes included, fishing charters and jet ski rental on request, resort water taxi, pets welcome

• Attractions: Theater of the Sea, Robbie’s Marina, Founders Park, the Islamorada sandbar and the reef dives offshore

Cottages, Casitas and Four Villas With a Butler

The five categories are genuinely different, not a naming exercise. Beachfront Cottages and Casitas put you on the sand and are what most people picture when they book. Coastal Villas and the Tropical Garden Suites sit back in the greenery, quieter and better value for a longer stay. Ocean Suites split the difference. Four of the villas come with butler service, which shifts the property into another bracket entirely for a family reunion or a small group travelling together. Say what you want when you book: the gap between a garden suite and a beachfront cottage is the gap between two different holidays.

SIDECAR, the Water Taxi and the Rest of the Collection

SIDECAR handles the daytime, tiki-bar style, drinks and light plates without leaving the beach. Dinner is where the collection earns its keep: the resort water taxi runs between La Siesta and its two sister properties, Amara Cay and Three Waters, which between them put a dozen kitchens within reach by boat. Arriving at dinner by water rather than by car is a small pleasure that never gets old, and it makes the wine list a rather easier decision.

Before You Book

Reserve a dock slip at the same time as the room if you are bringing a boat; they are finite and go early in season. Ask which building your category sits in, because beach proximity varies considerably across the property. Dogs are welcome, worth confirming at reservation. And plan at least one evening around the water taxi: people who never use it end up eating in the same place all week, which is not the point of staying here.